Will Ferrell, Harper Steele, Kristen Wiig Make Oscar Cut With ‘Will & Harper’

When Will & Harper made the Oscar shortlist for Documentary Feature, director Josh Greenbaum told Deadline, “I am just absolutely thrilled, and I know I share that emotion with Will and Harper, and the whole team behind the film. Obviously, when you work on something for years, and then you go off and edit it in a dark room with your editor, you never totally know how something is going to be received once you put it out into the world.”

But then acceptance has always been the theme of Will & Harper — acceptance of self, acceptance of family and friends, and acceptance of the people you encounter in life.

Early in the nearly two-hour film, protagonist Harper Steele says with heartbreaking candor, “I love this country so much. I just don’t know if it loves me back right now.” 

As a 61-year-old, newly-transitioned woman, Harper felt the pull to travel America as she had done frequently before, and embarked on a cross-country road trip with her longtime friend, comedic actor Will Ferrell — who displays a winsome vulnerability and sense of humanity that audiences don’t often get a chance to see, or don’t choose to see, because his goofy roles in Elf and Anchorman: The Legend of Ron Burgundy are so iconic. The real-life friendship between Will and Harper goes back three decades, to 1995, and the hallowed halls of Saturday Night Live, where Harper was a writer, and Will, a newbie cast member.

Equal parts road movie, buddy film and self-discovery drama, Will & Harper was shot during the pandemic in 2021, with the pair traveling from New York to Los Angeles in a vintage Jeep Grand Wagoneer. They shop at Walmart, hoist beers with locals and mow through countless cans of sour cream and onion-flavored Pringles. In Iowa City, Harper visits her childhood home. In Meeker, Oklahoma, she finds unexpected acceptance at a biker bar. But in Amarillo, Texas, things take a darker turn when the crowd becomes hostile during a night out at a steakhouse. The incident threatens not only Harper’s sense of physical safety, but her emotional state. Throughout these moments, Will is her sometimes bumbling wingman and comedic foil. 

“Their love language is comedy. That’s how they’ve known each other for 30 years,” explains Greenbaum (Barb and Star Go to Vista Del Mar, Strays). “It was important to them that whoever the filmmaker was, they would have an understanding of comedy. It also helped that we actually all knew each other prior. This is my seventh doc project, and my first documentary where I’ve known my subjects beforehand.”

But that didn’t stop Greenbaum from being a little nervous about screening the film for Harper and Will.

“For me, as a documentary filmmaker, the scariest moment of the entire production is when I sit down for the first time to show them the movie,” he admits. “You shoot for 17 days, and then you give each other hugs and say, ‘Alright, I’ll see you in five months’ [when the edit is done]. You hope they don’t say, ‘Oh, don’t use that bit. Don’t show me crying.’ Or, ‘I slipped up and I said the wrong thing. Can you not show that?’ But they gave me virtually zero notes.”

When Will and Harper premiered at the Sundance Film Festival last January — almost a year to this day — it earned a lengthy standing ovation. A month later, Netflix acquired the movie. In turn, the movie accessed Netflix’s potential audience of 282 million subscribers.

“Their vast reach was hugely important to Will, and Harper and myself,” says Greenbaum. “We just want the most people in the world to see this.”

The director says the streamer’s PR and marketing team immediately tapped into the documentary’s uniqueness.

“The first time Netflix sent a trailer over, I said, ‘I love it.’ That’s the first time in my career that’s ever happened. I usually have a lot of notes,” says Greenbaum. “They also understood the tone of the film, and the poster. From all of the marketing and outward-facing stuff, we’ve just been so aligned.”

Alignment was also in the stars when SNL alum Kristen Wiig penned a tune for the film, which she performs over closing credits. Her acoustic number, “Harper and Will Go West,” is also shortlisted for an Oscar in the category of Best Original Song.

“It’s pure Kristen Wiig. It’s funny, it’s sweet, it’s warm, it’s very much her,” says Greenbaum. “It also encapsulates the tone and feeling of the film. And as she says at the end, ‘A friend is a friend until the end.’ A beautiful, albeit simple sentiment, but one that bears repeating.”

Early awards support for Will & Harper is bucking the current trend of overlooking documentaries about entertainment figures. One hundred and sixty nine projects were eligible for the Oscar in the category of Documentary Feature, but only two with a celebrity tie-in  — Will & Harper and Eno (about musician and producer Brian Eno) — were selected for the 15-title shortlist. Despite much attention, movies about Celine Dion, Elton John, Martha Stewart, Luther Vandross, Pharrell Williams, and composer John Williams did not make the cut.

Also worth mentioning is the role political polarization may have played in the vote. With LGBTQ issues at the forefront of the 2024 presidential election, support for Will & Harper, and its message of tolerance and inclusion, may have been a way for Academy of Motion Picture Arts and Sciences members to push back against rising anti-trans rhetoric. 

And then there’s social media. Will and Harper aren’t active on digital platforms, but Greenbaum will occasionally scroll through posts and bring something to their attention that he finds compelling.

“I’ve been our conduit to let them know what the world is saying,” says the filmmaker. “Somebody wrote, ‘I recommended the documentary Will & Harper to a colleague who’s been struggling with her sister’s transition.’ She said, ‘I watched the program. It changed everything for me.’ Beautiful little stories like that are really uplifting for me to see. It’s creating bonds, and creating a language for people to have these difficult conversations.”

In the film, we see that even Will and Harper have awkward conversations. And some of the discussions they had with strangers on the road trip became lessons learned on both sides.

“We keep discovering over and over that it’s hard to hate up close,” Greenbaum concludes. “We just want that message to be heard and received by as many people as possible in America, but also around the world. We’re optimistic that it can change hearts and minds — not just for the trans community, but for any marginalized community.”